Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/016—Diazonium salts or compounds
  • G03F7/0163—Non ionic diazonium compounds, e.g. diazosulphonates; Precursors thereof, e.g. triazenes

Definitions

• This invention relates to photography and especially to positive-working and negative-working, diazo-sensitized photographic elements having particular utility in the photomechanical reproduction and photoresist arts.
• Photographic elements incorporating azide-sensitized light hardenable polymers are well known. Such negativeworking elements are prepared by coating a support with an azide sensitizer and a polymer. After exposure, the unhardened polymer is removed by solvent development, leaving an exposed, imagewise distribution of hydrophobic, ink-receptive polymer on the support material. Such developed photographic elements can, depending on the choice of support, choice of polymer and coating thickness, function as masters for lithographic printing, as masters for relief printing or as resist stencils for etching operations.
• the prior art also discloses negative-working systems which involve a base material coated only with a suitable diazo compound. Solvent development removes the unexposed material, forming a suitable master for lithographic printing.
• Positive-working photographic elements for photomechanical and photo-resist operations are also known in the art. Their preparation involves coating a base material with a diazo sensitizer-alkali-soluble polymer mixture in which the amount of sensitizer often equals the amount of polymeric material. Exposure to light increases the alkali solubility of the initially alkali-soluble polymer, so that subsequent development in a dilute alkaline solution removes the more alkali-soluble polymer in the areas of exposure. The undisssolved polymer image is a positive reproduction of the original pattern, and such a developed photographic element can produce positive copies by photomechanical means.
• an object of this invention is to provide novel diazo sensitizers which are advantageously employed in light-sensitive photographic elements designed particularly for the preparation of printing masters and for the preparation of photoresist stencils.
• Still another object of the present invention is to provide novel positive-working photographic elements utilizing substantially non-alkali soluble polymers.
• Yet another object of the instant invention is to provide new photographic masters for lithographic printing.
• Still another object of this invention is to provide novel photographic masters for relief printing.
• An additional object of the present invention is to provide new photoresists for etching purposes.
• Yet an additional object of this invention is to provide a novel photographic process for preparing masters for lithographic and relief printing.
• Still another object of the instant invention is to provide a new photographic process for preparing photoresist stencils.
• Another object is to provide a novel diazo compound.
• the objects of this invention are accomplished with a 1,2-diazoketone trihalomethane.
• the present 1,2 diazoketone trihalomethanes are light-sensitive and when coated on a support, they function advantageously in both negative-working and positive-working photographic elements.
• the 1,2-diazoketone trihalomethanes described herein can be coated either alone or in combination with a polymer such as gelatin or a polyester, a polyamide or the like, including mixtures thereof.
• 1,2-diazoketone trihalomethanes of this invention include those having a formula selected from:
• R is a trihalomethyl radical
• Z and Z represent the atoms necessary to complete a nucleus having at least 9 atoms and typically 9 to 18 atoms.
• R is a trihalomethyl radical and R is either a halogen atom or a lower alkyl radical.
• Lower alkyl radicals as comprehended herein include branched and straight chain substituted and unsubstituted alkyl radicals having from 1 to 6 carbon atoms an preferably from 1 to 4 carbon atoms.
• Preferred 1,2-diazoketone trihalomethanes include 5,6-dihydro-6-diazo-2-tribromomethyl quinoline-S- one, -bromo-8-diazo-7,8-dihydro-2-tribromomethyl quinoline-7-one, 5,6-dihydro-5-diazo '8 bromo-Z-tribromomethyl quinoline-6-one, 6-diazo-6,7-dihydro-2-tribromomethyl benzothiazole-7-one, 5,6-dihydro 6 diazo-Z-trichloromethyl quinoline-S-one, and 5,6-dihydro-6-diazo-8- methyl-Z-tribromomethyl quinoline-S-one.
• the above described 1,2-diazoketone trihalomethanes can be coated from solution upon a support material to provide a negative-working photographic element which is advantageously employed in photomechanical reproduction, especially lithographic printing. No additional polymeric material is required in the light-sensitive layer. Additionally, no solvent development step is required. Upon an imagewise exposure to actinic light, a print-out image is obtained in the exposed areas. This image is hydrophobic and readily accepts a greasy printing ink. Hydrated, unexposed areas do not accept the ink, and the exposed photographic element produces a highly acceptable master for lithographic printing.
• the nature of the support for the photographic element can be widely varied. Particularl useful supports are those porous supports, such as paper, to whose surface the light-sensitive trihalomethane derivative can be readily adsorbed.
• Coating thickness for the above described negativeworking elements can be widely varied but is typically thin, generally varying between about .1 mil and 3 mils. The only restrictions imposed, however, are the technological limitations imposed by the present state of advancement of the coating art.
• the method of coating can be any known by those skilled in the art. Whirler coating, dipping, swabbing, hopper coating and doctor blade coating, for example, are all suitable techniques.
• a second type of negative-working photographic element which is particularly suited to relief printing operations is produced by coating a support material with a mixture of the 1,2-diazoketone trihalomethane and gelatin.
• the percentage of light-sensitive trihalomethane to gelatin can vary considerably, with a range of from about 5 percent to about 50 percent, based on the total weight of both trihalomethane and gelatin, being typically employed.
• Coating of the second type of negative-working element can be accomplished by any of the techniques noted above.
• the choice of support can be widely varied. In this instance, however, more highly absorptive support materials are not to be preferred over other supports, since the gelatin functions in part as a binder.
• Coating thickness can be widely varied, with thicknesses of from less than 1 mil to over 7 mils being advantageously employed. For relief printing purposes, coating thickness of between about 3 and about 5 mils, are preferred.
• An imagewise actinic light exposure through an original pattern renders the exposed element oleophilic and hydrophobic in the areas of exposure.
• Development in warm water generally at least about 90 F., dissolves away the coated layer in the unexposed areas, producing a printing plate which reproduces a negative image of the original pattern.
• the present diazoketone trihalomethanes are also advantageously employed in positive-working photographic elements, wherein a support is coated with a light-sensitive layer that includes the trihalomethane as a sensitizer and a substantially alkali-insoluble polymer component.
• a support is coated with a light-sensitive layer that includes the trihalomethane as a sensitizer and a substantially alkali-insoluble polymer component.
• a wide variety of polymers can be advantageously employed in the positive-working photographic elements described herein.
• Suitable polymers include such unsaturated polyesters derived from polyols and unsaturated polycarboxylic acids as are described in the copending application of Mench et al. Photographic Element and Process, Ser. No. 693,710, filed Dec. 27, 1967 and currently copending herewith.
• Polyols which are advantageously employed in producing the polyesters utilized in this invention include both aliphatic and alicyclic polyols.
• Suitable a iphatic polyols can be, for example, such polyhydroxy compounds as lower alkane glycols having from 1 to 6 carbon atoms and homopolymers or copolymers of hydroxy substituted lower alkyl acrylate esters wherein the alkyl moiety has from 1 to 6 carbon atoms.
• Specific aliphatic polyols which exhibit particular utility in preparing the subject polyesters are, for example, ethylene glycol, 2,2-di(4-hydroxyethylphenyl)-propane, neopentyl glycol, polyvinyl alcohol and poly or copoly acrylates wherein at least part of the acrylate is a hydroxy-alkyl acrylate such as poly(hydroxyethylacrylate) and copoly(hydroxyethylacrylatermethylacrylate).
• Alicyclic polyols suitably employed in preparing the subject polyesters include cyclic alkanes having from 5 to 7 atoms in the carbocyclic nucleus, 1,4-dihydroxymethylcyclohexane for example, and polyhydroxycontaining carbohydrates such as cellulosic compounds including substituted cellulose derivatives of which hydroxy-propyl cellulose is an example.
• Unsaturated carboxylic acids which can be advantageously employed in the practice of this invention include wherein Z represents the atoms necessary to form an unsaturated bridged or unbridged carbocyclic nucleus typically having 6 to 7 carbon atoms. Such a carbocyclic nucleus can be substituted or unsubstituted.
• Particularly suitable acid units are 4-cyclohexene-1,2-dicarboxylic acid, 5-norbornene-2,3-dicarboxylic acid, hexachloro- 5[2:2:l]bicycloheptane-Z,S-dicarboxylic acid and the like.
• Such unsaturated polycarboxylic acids readily polycondense with the above described polyols to form the polyesters useful in preparation of the present light-sensitive compositions. Mixtures of more than one polyol or more than one unsaturated polycarboxylic acid can be used.
• the subject polyesters are of two varieties, either essentially straight chain copolymers of a monomeric polyol and one of the unsaturated acids of this invention or copolymers incorporating an initially polymeric polyol and the subject acid units as side chains.
• polyesters include, for example, the esterification products of: polyvinyl alcohol and cis-4-cyclohexene-1,2- dicarboxylic acid; cellulose and cis 4 cyclohexene 1,2- dicarboxylic acid; hydroxypropylcellulose and cis-4-cyclohexene-l,2-dicarboxylic acid; polyvinyl alcohol, benzoyl chloride and cis-4-cyclohexene 1,2 dicarboxylic acid; methyl acrylate/hydroxyethyl acrylate copolymer and cis-4-cycl0hexene-1,2-dicarboxylic acid; the polycondensation product of ethylene glycol and cis-4-cyclohexene- 1,2-dicarboxylic acid; and ethylene glycol, cis-4-cycloheXene-1,2-dicarboxylic acid and hexachloro-5-[2:2:1]- bicycloheptene 2,3
• R and R are each either a hydrogen atom or a lower alkyl radical, R is a lower alkyl radical, R is either a lower alkyl radical or a radical having the formula -OH OOR (wherein R is a lower alkyl radical) and X is o CH2CH2COR1 (wherein R is a lower alkyl radical) or a lower alkyl radical or a hydrogen atom.
• These alcohol-soluble acryloylpeptide derivative polymers can also be copolymers of the above mentioned acryloylpeptide units with at least one recurring unit having the formulas:
• R is either a lower alkyl radical or a hydrogen atom, and both R and R are lower alkyl radicals.
• a copolymer is, for example, copoly(methylacrylate, N- acry1oylN'-butyl-glycinamide). Additionally, mixtures of the polyesters and other polymers described herein are advantageously used as the polymer component.
• the preparation of a positive-working photographic element is accomplished by solvent coating a combination of a polymer and a 1,2-diazoketone trihalomethane sensitizer on a support material.
• a coating solvent varies between polymers, but all such solvents are easily determined by one skilled in the art. Coating can be accomplished by any means. Whirler coating, dipping, swabbing, hopper coating and doctor blade coating are examples of suitably employed techniques.
• the amount of the 1,2-diazoketone trihalomethane sensitizcr can be widely varied, with from about 5 percent by weight to over 40 percent by weight of the accompanying polymer being illustrative. Typically, between 10 and 30 weight percent of sensitizer to polymer component is preferred.
• the total weight of sensitizcr and polymer can also be widely varied, with about 2 percent by Weight to over 30 weight percent of the final coating solution being illustrative.
• the particular percentage of solids in any given coating is dependent upon the use to which the photographic element will be applied.
• Coating thickness is also a function of intended use, and its limits are only those imposed by the concentration of the coating solution and the state of advancement attained by the coating art. Generally, however, coating thicknesses of between 1 mil and 4 mils are employed.
• the choice of support upon which the sensitized polymer for positive-working systems is coated can be widely varied and is typically a function of that use to which the developed photographic element will be applied.
• Metal laminates, where a thin layer of a metal such as copper is bonded to a polymeric base material, are particularly suitable where subsequent etching is involved, such as in the production of printed circuits.
• the substantially alkali insoluble polymers are rendered suitably soluble (in the areas of exposure) in dilute alkaline solutions such as sodium and potassium hydroxide or trisodium phosphate.
• the positive-working photographic elements containing polymers is carried out with a dilute aqueous alkaline solution, such as those noted above, and which alkaline solution is susceptible of a wide variation in concentration.
• the alkaline developing solutions vary from about 1 to 20 weight percent of alkaline material to total solution, with the need for one concentration, rather than another, depending upon polymer concentrations, coating thickness and intensity of exposure. The concentration can be more extensively varied, however, in accordance with usual practices.
• Treatment of the exposed element with developer solution causes the highly alkali soluble material in the exposed areas to dissolve away. This developing treatment can be accomplished by dipping, spraying, swabbing, and other techniques which permit the developer solvent to contact the exposed element for a period of time sufiicient to selectively dissolve away the alkali-soluble polymer in the areas of exposure.
• the polymer-containing positiveworking photographic element bears a polymer image which is a positive reproduction of the original pattern.
• This image is hydrophobic and ink receptive, and such developed photographic elements function advantageously in photomechanical reproduction operations as masters for lithographic printing and as masters for relief printing. They also function as resist stencils for etching operations and the like.
• Support materials for all of the above described photographic elements can be metals, such as copper, aluminum, zinc and the like. They can also be conventional photographic film bases such as cellulose nitrate, polystyrene, cellulose acetate, cellulose acetate butyrate, poly(ethylene terephthalate), paper including polyethylene-coated and polypropylene-coated paper, and the like. Other support materials are well known in the prior art.
• EXAMPLE 1 5,G-dihydro-6-diazo-2-tribromomethylquinoline 5-one is prepared from an intermediate, 6-acetamido-5-bromo- 2-tribromomethylquinoline, which in turn is prepared from 6-acetamidoquinaldine.
• a mixture of 6-acetamidoquinaldine, (21.0 g.) (Hamer, J. Chem. Soc. 119, 1435) and anhydrous sodium acetate g.) in glacial acetic acid (210 ml.) is heated to 70 C. and a solution of bromine (67.2 g.) in glacial acetic acid (90 ml.) is added over 30 minutes with stirring.
• EXAMPLE 2 5 bromo 8 diazo-7,8-dihydro-2-tribromomethylquinoline-7-one is prepared from an intermediate, 8-acetamide-5,7-dibromo-2-tribromomethylquinoline which in turn is prepared from S-acetamidoquinaldine, each preparation being according to the procedure of Example 1. except that 8-acetamidoquinaldine (7 g.) is mixed with anhydrous sodium acetate (30 g.) in glacial acetic acid (74 ml.) and after heating to 70 C., a solution of bromine (28 g.) in glacial acetic acid (24 ml.) is added according to the method of Example 1.
• EXAMPLE 3 5,6 dihydro 5 diazo 8 bromo 2 tribromomethylquinoline-6-one (M.P. 1536 C. with decomposition) is prepared from 6 g. of an intermediate, 5-acetamido-6,8- dibromo-Z-tribromomethyl quinoline (M.P. 221-2 C.), which is in turn prepared from 7 g. of S-acetamidoquinaldine. All preparations are as described in Example 2.
• EXAMPLE 4 6 diazo 6,7 dihydro-2-tribromomethylbenzothiazole- 7-one (M.P. 1446 C. with decomposition) is prepared from 3 g. of an intermediate, 6-acetamido-7-bromo-2-t1'ibromomethylbenzothiazole (M.P. 158-60" C.), which is in turn prepared from 21.6 g. of 6-acetamido-2-methylbenzothiazole. All preparations are as described in Example 1.
• EXAMPLE 5 5,6-dihydro-6-diazo-2-trichloromethylquinoline-S-one is prepared from an intermediate, 6-acetamido-5-chloro- 2-trichloromethy1 quinoline, which in turn is prepared from 6-acetamidoquinaldine.
• a mixture of 6-acetamidoquinaldine (5.25 g.) and anhydrous sodium acetate (22.5 g.) in glacial acetic acid (80 ml.) is heated to 60 C. and chlorine gas is passed into the stirred solution. When excess chlorine is present, the temperature is raised to 95 C. and heating continued for 90 minutes.
• the reaction mixture is placed in water and the precipitated sticky solid is filtered off.
• 6-acetamido-5-chloro-2-trichloromethyl quinoline (5 g.), M.P. 213-4" C.
• 6-acetamido-5-chloro-2-trichloromethyl quinoline (3 g.) is dissolved in 98% concentrated sulfuric acid (6 ml.) and heated on a steam bath for 10 minutes with stirring. The mixture is cooled to room temperature and solid sodium nitrite (0.62 g.) is added. The mixture is stirred for a further 60 minutes at room temperature and then poured onto ice (33 g.) The clear solution is kept for minutes at 0 C. and then aqueous sodium acetate is added until the solution has a pH of 4. The yellow precipitate is filtered off and crystallized from alcohol to yield 1.8 g. of 5,6-dihydro-6-diazo-2-trichloromethylquinoline-S-one, M.P. 157 C. with decomposition.
• EXAMPLE 6 The following series of reactions is employed to prepare 5,6 dihydro-6-diazo-8-methyl-2-tribromomethyl quino- 1ine-5-one. 2,8-dimethyl-6-nitroquinoline (43.2 g.) is reduced with stannous chloride dihydrate (270. g.) in concentrated hydrochloric acid using the method of Hamer (J. Chem. Soc. 119 1435) to give the 6-amino derivative (34 g.) which is recrystallized from methanol to give pure material, M.P 1635 C.
• EXAMPLE 7 5,6 dihydro-6-diazo-2-tribromomethylquinoline-S-one (0.05 g.) is dissolved in dichloromethane (5 ml.) and the solution impregnated onto filter paper and dried. The sample is exposed through an original pattern for 60 seconds to a watt U.V. lamp held 18 inches from the exposing plane. The sample is then washed with water. In the exposed areas a print-out image is obtained which is water repellant and accepts a greasy lithographic printing ink. The wet unexposed areas do not accept the greasy ink.
• EXAMPLE 8 A solution of 5,6-dihydro-6-dihydro-6-diazo-2-tribromomethyl-quinoline-5-one (0.1 g.) in dichloromethane (3 ml.) and dibutylphthalate (0.5 ml.) is added to a 10% aqueous solution of pigskin gelatin (10.0 ml.) containing sodium triisopropyl-naphthalenesulphonic acid (0.5 ml. of a 5% solution) and saponin (0.5 ml. of a 15% solution) as dispersion and coating aids. A uniform dispersion is obtained by treating the mixture for 5 minutes in a mixing blender.
• the dispersion is coated at a 4 mil thickness onto triacetate film base and is allowed to dry.
• the coating is then exposed for 2 minutes through an original pattern to a 125 watt U.V. lamp held 18 inches from the exposing plane.
• the exposed sample is washed with water at 35 C. which causes the gelatin in the unexposed areas to dissolve away. A negative gelatin relief image is obtained.
• EXAMPLE 9 A sheet of flexible poly(ethylene terephthalate) copper laminate is whirler coated at 200 rpm. with the following solution:
• the coated layer after drying, is exposed for 2 minutes through an original pattern to 4, 125 watt high pressure mercury vapor lamps, rich in ultraviolet light, placed 18" from the exposing plane. Development is carried out by immersing the exposed photographic element in 1% sodium hydroxide for 20 seconds, followed by a water rinse and light swab with cotton wool. During development the exposed areas are removed, thus leaving a positive resist stencil which withstands 3 mins. etching in 38 degrees B. ferric chloride.
• EXAMPLE 10 A sheet of the flexible laminate of Example 4 is whirler coated as outlined in Example 4, but with the following composition:
• Example 9 The dried coating, although slightly tacky, is exposed as in Example 9 for 2 minutes after which it is developed by immersion in a swabbing with a trisodium phosphate solution. A positive polymer image is obtained, the polymer in the exposed areas being dissolved away.
• the developed resist stencil withstands 3 mins. spray etching with 38 degrees B. ferric chloride as in Example 9.
• EXAMPLE 1 A sheet of flexible poly(ethylene terephthalate) copper laminate is whirler coated as in Example 9. To overcome tackiness of the layer produced in Example 10, a mixture of polyamide and polyester is used as follows:
• EXAMPLE 12 A sheet of flexible poly(ethylene terephthalate)-copper laminate is coated as in Example 4, but with the following solution:
• Example 10 The dry, non-tacky layer is exposed and developed as in Example 10.
• the exposed areas are more difficult to remove than in the previous examples.
• Excellent results are obtained when the developed resist stencil is etched with ferric chloride as in Example 9.
• EXAMPLE 13 A sheet of anodized aluminum is whirler coated at 200 r.p.m. with the following solution:
• Copolyester of ethylene glycol and cis-4-cyclohexene-1,2- dicarboxylic anhydride (7 parts by weight) and hexach1oro(2:2:1)bicycloheptene dicarboxylic anhydride (1 part by weight)0.7 g.
• a photographic element comprising a support having coated thereon a light-sensitive layer comprising a 1,2- diazoketone trihalomethane having a formula selected from the group consisting of:
• R is a trihalomethyl radical and Z and Z in combination with the atoms to which they are attached in said formula form a quinoline or benzothiazole nucleus.
• a photographic element as described in claim 1 wherein the 1,2-diazoketone trihalomethane has a formula selected from the group consisting of (1) about 50 to about percent by weight of gelatin,
• diazoketone trihalomethane having a formula selected from the group consisting of:
• R is a trihalomethyl radical and Z and Z in combination with the atoms to which they are attached in said formula form a quinoline or benzo thiazole nucleus.
• R is a trihalomethyl radical and Z and Z in combination with the atoms to which they are attached in said formula form a quinoline or benzo thiazole nucleus.
• R is a trihalomethyl radical and R is selected from the group consisting of a halogen atom and a lower alkyl radical.
• a photographic element as described in claim 4 wherein the 1,2-diazoketone trihalomethane is selected from the group consisting of:
• R is a trihalomethyl radical and Z and Z in combination with the atoms to :which they are attached in said formula form a quinoline or benzothiazole nucleus, and a substantially alkali-insoluble poymer that, in the presence of said 1,2-diazoketone trihalomethane, is rendered alkalisoluble on exposure to light.
• polymer component is a polyester derived from a polyol and an unsaturated polycarboxylic acid.
• (l) a polyol selected from the group consisting of lower alkane glycols, homopolymers and copolymers of polyhydroxy substituted lower alkyl acrylate esters, polyhydroxy substituted cyclic alkanes and polyhydroxy substituted carbohydrates, and
• Z represents the atoms necessary to form an unsaturated carbocylic nucleus having 6 to 7 carbon atoms.
• polyester poly(ethylene 4 cyclohexene- 1,2-dicarboxylate).
• R is a lower alkyl radical
• R is selected from the group consisting of:
• R is a lower alkyl radical
• R is selected from the group consisting of:
• R is a lower alkyl radical; (2) a lower alkyl radical, and (3) a hydrogen atom; and (II) copolymers comprising from 10 to 75 mole percent of at least one of said acryloylpeptide units and from 25 to mole percent of at least one recurring unit having a formula selected from the group consisting of:
• R is selected from the group consisting of:
• R is a trihalomethyl radical and R is selected from the group consisting of a halogen atom and a lower alkyl radical.
• a photographic element as described in claim 7 wherein the 1,2-diazoketone trihalomethane is selected from the group consisting of:
• a photographic element comprising a support having coated thereon a light-sensitive layer comprising a substantially alkali insoluble polymer component that, in the presence of a 1,2-diazoketone trihalomethane, is rendered alkali soluble on exposure to light, said polymer component having at least one polymer selected from the group consisting of (I) polyester derived from:
• R is selected from the group consisting (a) a hydrogen atom and (b) a methyl radical; (2) R is a lower alkyl radical; (3) R is selected from the group consisting (a) an alkyl radical having up to seven carbon atoms, and (b) a radical having the formula wherein R is a lower alkyl radical; (4) R is selected from the group consisting (a) a hydrogen atom, and (b) a lower alkyl radical; (5) X is selected from the group consisting wherein R is a lower alkyl radical; (b) a lower alkyl radical, and (c) a hydrogen atom; and (B) copolymers comprising from 10 to 75 mole percent of at least one of said acryloylpeptide units and from 25 to mole percent of at least one recurring unit having a formula selected from the. group consisting of:
• R is selected from the group consisting (a) a hydorogen atom, and (b) a lower alkyl radical; and (2) R and R are each lower alkyl radicals,
• l,2-diazoketone trihalomethane having a formula selected from the group consisting of:
• a photographic element comprising a support having coated thereon a light-sensitive layer comprising:
• a photographic process for treating an imagewise exposed photographic element comprising a support having coated thereon a light-sensitive layer containing a 1,2-diazoketone trihalomethane having a formula selected from the group consisting of:
• R is a trihalomethyl radical and Z and Z, in combination with the atoms to which they are attached in said formula form a quinoline or benzothiazole nucleus to produce a lithographic master for photomechanical reproduction, which process comprises contacting said photographic element with water for a period of time sufficient to selectively hydrate the light-sensitive layer in the unexposed areas.
• a photographic process for treating an imagewise exposed photographic element comprising a support having coated thereon a light-sensitive layer containing (1) about 50 to about 95 percent by weight of gelatin,
• diazoketone trihalomethane having a formula selected from the group consisting of:
• R is a trihalomethyl radical and Z and Z; in combination with the atoms to which they are attached in said formula form a quinoline or benzothiazole nucleus, which process comprises contacting said photographic element with water for a period of time sulficient to selectively hydrate the light-sensitive layer in the unexposed areas.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
• Quinoline Compounds (AREA)

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Cited By (10)

• 1967
  • 1967-03-31 GB GB1495367A patent/GB1230771A/en not_active Expired
• 1968
  • 1968-03-20 US US714415A patent/US3592646A/en not_active Expired - Lifetime
  • 1968-03-29 DE DE19681772100 patent/DE1772100A1/de active Pending
  • 1968-04-01 FR FR1589401D patent/FR1589401A/fr not_active Expired
  • 1968-04-01 BE BE713072D patent/BE713072A/xx unknown

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